US3663974A - Treatment of a cross-linking agent-impregnated cellulosic fabric with a gaseous acid catalyst - Google Patents
Treatment of a cross-linking agent-impregnated cellulosic fabric with a gaseous acid catalyst Download PDFInfo
- Publication number
- US3663974A US3663974A US711136A US3663974DA US3663974A US 3663974 A US3663974 A US 3663974A US 711136 A US711136 A US 711136A US 3663974D A US3663974D A US 3663974DA US 3663974 A US3663974 A US 3663974A
- Authority
- US
- United States
- Prior art keywords
- fabric
- percent
- formaldehyde
- aldehyde
- treatment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004744 fabric Substances 0.000 title claims abstract description 188
- 238000004132 cross linking Methods 0.000 title description 5
- 239000003377 acid catalyst Substances 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 84
- 230000002378 acidificating effect Effects 0.000 claims abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 34
- 238000005804 alkylation reaction Methods 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 23
- 230000029936 alkylation Effects 0.000 claims description 14
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 238000005470 impregnation Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 229920002678 cellulose Polymers 0.000 abstract description 6
- 239000001913 cellulose Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000004902 Softening Agent Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 239000007789 gas Substances 0.000 description 28
- 150000001299 aldehydes Chemical class 0.000 description 25
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 239000000835 fiber Substances 0.000 description 16
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 13
- 229920000742 Cotton Polymers 0.000 description 12
- -1 linen Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010306 acid treatment Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 238000004900 laundering Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- DZNJSBHVDXLTIK-UHFFFAOYSA-N 1-(hydroxymethyl)imidazolidine-2,4-dione Chemical compound OCN1CC(=O)NC1=O DZNJSBHVDXLTIK-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005517 mercerization Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
- D06M11/54—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur dioxide; with sulfurous acid or its salts
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
- D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/123—Polyaldehydes; Polyketones
Definitions
- An additional object of this invention is to provide a method of producing a wash and wear fabric having soft and smooth hand.
- the process of this invention is applicable to fabrics containing cellulosic fibers (either natural or artificial) alone or as mixtures of two or more in various proportions or as mixtures with other fibers.
- natural cellulosic fibers cotton, linen, hemp, etc. may be exemplified, and among artificial cellulosic fibers are, for example, viscose rayon, cupra ammonium rayon and other regenerated cellulosic fibers.
- Other fibers which may be used with one or more of the above mentioned cellulosic fibers are, for example, cellulose acetate, polyamides, polyesters, polyacrylonitriles, polyolefines, polyvinyl chlorides, polyvinylidine chlorides, polyvinyl alcohols fibers. ll desired the fibers may be those graft-copolymerized with eopolymeriierec vinyl monomers.
- the fabric may be knit, woven or non-woven, or be any otherwise constructed fibric.
- a fabric is first impregnated with an aqueous liquid containing an aldehyde or a substance which is capable of liberating an aldehyde under the treating condition, such as paraform, methylol hydantoin, glyoxal, glutal aldehyde, acetal, hexamethylene, tetramine, etc.
- an aldehyde or a substance which is capable of liberating an aldehyde under the treating condition such as paraform, methylol hydantoin, glyoxal, glutal aldehyde, acetal, hexamethylene, tetramine, etc.
- formaldehyde is most preferred in this invention.
- an aldehyde e.g. formaldehyde, glyoxal
- a substance capable of liberating an aldehyde is applied to a fabric in the form of aqueous solution or liquid by any suitable manner such as by spraying the liquid on the fabric or immersing the fabric in the liquid followed by squeezing.
- the fabric to be subjected to the subsequent gaseous acid treatment should contain about i 25 percent, preferably 4 15 percent by weight of an aldehyde (as available component) or an aldehyde-liberating compound (as available aldehyde) based on the weight of the fabric.
- an aqueous liquid containing from 1 to 50 percent (usually 5 20 percent) by weight of an aldehyde (as available component) or containing an aldehyde-liberating substance in such an amount that it would liberate an aldehyde in a concentration of from 1 to 50 percent (usually 5 20 percent) by weight in the liquid is employed.
- the liquid is applied to the fabric by spraying or dipping so that the fabric has a wet pick-up of 50 100 percent (usually 60 percent) by weight. If necessary, the fabric is squeezed to attain the pick-up recited above.
- the solution of an aldehyde or an aldehyde-liberating substance contains a formaldehyde (or aldehyde) catcher.
- the term catcher as an is intended to mean a substance which is capable of holding or retaining formaldehyde (or an aldehyde) during drying and subsequent acid treating stage to prevent the dissipation of the aldehyde.
- aldehyde catcher are polyacrylates such as polyethylacrylate, polybutylacrylate, polyethyl-butylacrylate, polyhydroxyethylacrylate, etc. and cellulose ethers such as methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, etc.
- polyacrylates and cellulose ethers are commercially available as aqueous solution or emulsion of solid content of 20 to 40 percent.
- aqueous solution or emulsion of solid content of 20 to 40 percent.
- such an emulsion or solution is added to the liquid containing the aldehyde or an aldehyde-liberating substance so as to be in a concentration of from 1 to 10 percent (as such emulsion or solution) by weight.
- the solution may also contain a small amount of suitable blueing agent, brightening agent, softener (lubricant), etc.
- a softener or lubricant will affect the wash and wear properties and strength of the fabric resulting from the treatment according to this invention.
- preferable softeners or lubricants are polyolefine type softeners such as polyethylene, polypropylene, etc. and silicone type softeners such as those commercially available under the trade mark Noran Silicone Softener. These softeners will impart to the fabric desirable soft hand, good wash and wear properties and desired balance of dry and wet resilience and strength of the fabric. It is most preferable to employ a polyolefine type softener and a silicone type softener together.
- the fabric After impregnated with the liquid containing an aldehyde or an aldehyde-liberating substance, the fabric is contacted with gaseous hydrochloric acid, sulfur trioxide or sulfur dioxide and subjected to an acetalizing or cross-linking reaction between the cellulose and aldehyde.
- gaseous hydrochloric acid, sulfur trioxide or sulfur dioxide As mentioned before the moisture (calculated as water) content of the fabric during the contact with gaseous HCl, 80;, or S0 and the reaction should be so controlled as to be below 20 percent by weight based on the fabric weight. Therefore, it is usually necessary that the fabric is dried before the acid treatment so that the fabric, when entering in the gaseous acid treating stage, has a moisture content within the required range, namely 3 20 percent (preferably 6 15 percent).
- the fabric may be dried in any suitable manner at a temperature from room temperature up to about 120 C.
- the fabric with the above mentioned moisture content is then contacted with the gaseous acid (catalyst for the reaction between the aldehyde and cellulose).
- the gaseous acid catalyst for the reaction between the aldehyde and cellulose.
- This is accomplished by contacting or exposing the fabric to an atmosphere containing the gaseous acidic substance.
- the atmosphere to be contacted with the fabric should contain 1 100 percent by volume, preferably 5 40 percent by volume, of gaseous hydrogen chloride, sulfur trioxide or sulfur dioxide and be maintained at a temperature below 50 C., preferably between about C. and 50 C.
- the acidic substance or catalyst is applied to the fabric because the gas is penetrated or dispersed into and absorbed by the fabric.
- any suitable means may be employed.
- an open vessel containing hydrochloric acid in a desired concentration is placed at the bottom of a closed chamber and the said container is heated so that gaseous hydrogen chloride vaporized from the container will fill the interior of the chamber through which the fabric may be passed.
- hydrogen chloride gas or sulfur dioxide or trioxide gas as separately prepared may be continuously introduced into a closed chamber through which the fabric may be passed.
- a fabric is contacted with a continuously travelling porous belt impregnated with hydrochloric acid of a desired concentration so that during the contact with the belt the fabric is applied with hydrogen chloride gas developed from the hydrochloric acid within the belt. In this case, care should be taken that the fabric would not directly contact with the hydrochloric acid liquid contained in the belt.
- the contact of the fabric with gaseous hydrogen chloride, sulfur dioxide or sulfur trioxide should be effected at a temperature below 50 C., preferably between 20 C. and 50 C.
- the time during which the said contact is carried out varies very widely depending upon and is corelated with the temperature, particular acid employed, the concentration of acid in the atmosphere to be contacted with the fabric. Hydrogen chloride or sulfur trioxide is more reactive and therefore requires shorter treating time and/or lower temperature than sulfur dioxide. When the acid concentration in the atmosphere to be contacted with the fabric is higher, a shorter time and/or lower temperature may be employed.
- the contact should be such that the fabric absorbs the acidic catalyst in an amount sufficient to cause the desired acetalization or cross-linking reaction.
- the time for contacting the fabric with the gaseous acidic catalyst varies over a wide range, namely only one or few seconds to even 90 minutes or more, depending largely upon the concentration of the gas and the temperature at which the contact is carried out.
- the reaction between the aldehyde and cellulose is commenced.
- the desired reaction may be completed while contacting the fabric with the gas.
- the atmosphere to be contacted with the fabric may contain, in addition to the gaseous acid, other gaseous components such as air, nitrogen gas and moisture (water) which do not affect the reaction involved.
- the moisture condition in the treating atmosphere may be neglected in connection with the moisture content of the fabric mentioned before.
- the fabric should be kept at its open width because the creases or wrinkles formed on the fabric during the process are difficult to be removed or recovered and lead to critical loss in the marketability of the product.
- the fabric is washed to remove any acid and free material remaining on the fabric. The washed fabric is then dried.
- a cellulosic fabric may be subjected to the method of this invention without any pretreatment of the fabric.
- the mercerization is well known in the art and no detailed explanation thereabout would be necessary.
- alkylation or substituted-alkylation may be carried out in a conventional manner by treating the fabric with an alkylation (or substituted-alkylation) agent in the presence of an alkaline condition.
- an alkylation (or substituted-alkylation) agent in the presence of an alkaline condition.
- dialkyl sulfate e.g. dimethyl sulfate, diethyl sulfate
- alkyl or substituted alkyl halide e.g.
- butyl chloride, ethyl chloride, butyl bromide, ethyl bromide; ethylene chlorohydrine, ethylenebromohydrine, chloroacetic acid, bromoacetic acid, etc. may be used as alkylation or substituted-alkylation agents.
- ethylene oxide, propylene oxide or the like may be employed.
- a fabric is impregnated with an aqueous solution (5 percent by weight or more in concentration) of the alkylation (or substituted alkylation) agent and squeezed.
- the fabric is further impregnated with a strong percent by weight or more) aqueous alkali solution, for example, of sodium hydroxide or potassium hydroxide, and then squeezed.
- a strong percent by weight or more aqueous alkali solution for example, of sodium hydroxide or potassium hydroxide
- the alkylation or substituted-alkylation agent is insoluble in water it may be applied to the fabric in the form of emulsion.
- the alkylation or substituted alkylation agent is reactive with water it may be applied to the fabric in the form of a solution in an organic solvent for example, alcohol or benzene.
- the alkylation or substituted-alkylation may be carried out on a conventional mercerizing machine. It is preferable that the alkylation or substituted-alkylation degree is such that 2 5 mols of alkyl or substituted alkyl groups are introduced per 100 glucose units constituting the fabric fibers.
- ASTM-D-l 295-53T indicated by the sum of values for fillings Wet resilience Dry resilience and warps. Wash and wear Determined by comparing with properties Monsanto Plastic Model. Tear strength ASTM-D-l424-56T (Elmendorf method) Laundry By AATCC Tentative Test Method 88-1960-4a.
- Example 2 The procedure of Example 1 was repeated except that the fabric, after the immersion in the formaldehyde solution and the subsequent drying, was passed through a chamber maintained at 20 C. for 15 minutes. Within the chamber and at the bottom thereof an open container had been placed containing 36 percent hydrochloric acid so that the chamber contains about 6 percent by volume of hydrogen chloride gas during the treatment of the fabric. Immediately after this hydrochloric treatment, the fabric was washed sufficiently with water and dried. The treated fabric was tested and the results are given in the following table. In this table are also given the corresponding data in respect of a conventional resin finished fabric and also in respect of a conventional resin finished fabric and also in respect of a conventional formaldehydetreated fabric, for comparison.
- EXAMPLE 4 A mercerized cotton poplin was immersed in an aqueous solution containing 13 percent of hexamethylene tetramine, 2 percent of Noran Silicone Softener (a silicone type softener), 4 percent of polyethylene emulsion (solid content 20 percent) and 0.01 percent of a penetrating agent. The fabric was then squeezed to a wet pick up of 70 percent and dried at 1 10 C. to reduce the moisture content to l0 percent. Then the fabric was contacted for 20 minutes with a polystyrene sponge sheet impregnated with 36 percent hydrochloric acid and heated at 50 C. During this contact, the fabric was exposed to a gas containing 1 percent (by volume) of hydrogen chloride gas. Immediately after this hydrochloric treatment the fabric was washed and dried, and subjected to testing. The results were as follows:
- EXAMPLE 5 A mercerized cotton poplin was immersed into an aqueous liquid containing 35 percent of formaldehyde (37 percent), 2 percent of polyethylene emulsion (solid content 20 percent) and 2 percent of polyethyl-butylacrylate (solid 30 percent). Then the fabric was squeezed to a wet pick-up of 65 percent and dried to a moisture content of percent. The fabric wound up on a roller and placed within an autoclave in which was arranged a second winding roller spaced from the first roller. The air in the autoclave was replaced by sulfur dioxide so that the interior volume of the autoclave contains about 10 percent by volume of sulfur dioxide at 50 C.
- EXAMPLE 7 A mercerized cotton poplin was immersed in an aqueous solution containing 10 percent by weight of monochloroacetic acid, squeezed to a wet pick-up of 65 percent, then immersed in 30 percent aqueous solution of sodium hydroxide and squeezed to a wet pick-up of 70 percent, and the reaction was allowed to proceed for 2 minutes while holding the edges of the fabric to keep the same at the open width. Then the fabric was washed with water, neutralized, again washed and dried.
- EXAMPLE 10 A satin cloth composed of highly polymerized cellulosic fibers (so-called Polynosic” and sold by Toyo Spinning Co., Ltd. under the trade mark Tufcel") was immersed in an aqueous liquid containing 20 percent of formaldehyde (35 percent), 4 percent of polyethylene emulsion (solid 20 percent) and 2 percent of polyethyl-butylacrylate (solid 30 percent). Then the fabric was squeezed to a wet pick-up of 65 percent and dried at 100 C. to a moisture content of 12 percent. The fabric was passed through a closed chamber of an atmosphere containing 5 percent (by volume) of hydrogen chloride gas at 50 C. for 30 seconds. Then the fabric was washed and dried, and tested. The test results were as follows:
- EXAMPLE 1 l A cotton poplin was immersed in an aqueous bath containing 35 percent of formaldehyde (38 percent), 4 percent of polyethylene emulsion (solid 20 percent) and 2 percent of Noran silicone softener. The fabric was squeezed to a wet pick-up of 70 percent and dried to 8 percent. The dried fabric was passed through a closed chamber maintained at 30 C. for seconds while feeding hydrogen chloride gas to the chamber so that the latter contains about 12 percent (by volume) of hydrogen chloride gas during the treatment. immediately often this treatment the fabric was washed and dried. The test results were as follows:
- a process of treating a cellulosic fiber-containing fabric to improve its wet and dry resilience which comprises impregnating the fabric with an aqueous liquid containing as the sole active fiber treating agent a compound selected from the group consisting of formaldehyde and formaldehyde liberating compounds in an amount of l-25 percent by weight based on the fabric weight, drying the fabric to a moisture content of 3-20 percent by weight and then contacting the dried fabric with a gaseous acidic substance selected from the group consisting of sulfur trioxide and sulfur dioxide, at a temperature below 50 C.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4315861 | 1961-11-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3663974A true US3663974A (en) | 1972-05-23 |
Family
ID=12656039
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US711136A Expired - Lifetime US3663974A (en) | 1961-11-28 | 1968-03-06 | Treatment of a cross-linking agent-impregnated cellulosic fabric with a gaseous acid catalyst |
Country Status (4)
Country | Link |
---|---|
US (1) | US3663974A (en, 2012) |
DE (1) | DE1444129C3 (en, 2012) |
GB (1) | GB980980A (en, 2012) |
NL (1) | NL286002A (en, 2012) |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3837799A (en) * | 1968-09-24 | 1974-09-24 | Cotton Inc | Process for creaseproofing cellulosic fiber-containing fabric using formaldehyde vapor and a solid and a solid catalyst |
US3841832A (en) * | 1971-12-06 | 1974-10-15 | Cotton Inc | Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide |
US3884632A (en) * | 1973-03-14 | 1975-05-20 | Mc Graw Edison Co | Continuous durable-press processing of fabric and garments |
US3951595A (en) * | 1974-07-10 | 1976-04-20 | Mcgraw-Edison Company | Vapor phase process for cellulose fabrics |
US4108598A (en) * | 1976-12-02 | 1978-08-22 | The Strike Corporation | Durable press process |
US4269602A (en) * | 1979-05-07 | 1981-05-26 | Riegel Textile Corporation | Buffered non-formaldehyde durable press textile treatment |
US4269603A (en) * | 1979-05-04 | 1981-05-26 | Riegel Textile Corporation | Non-formaldehyde durable press textile treatment |
USRE30860E (en) * | 1971-12-06 | 1982-02-02 | Cotton, Incorporated | Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide |
US4396390A (en) * | 1981-09-04 | 1983-08-02 | Springs Mills, Inc. | Aqueous formaldehyde textile finishing process |
WO1999010589A1 (en) * | 1997-08-22 | 1999-03-04 | Hiroharu Okamoto | Moisture-controlled curing durable press process |
US5885303A (en) * | 1997-05-13 | 1999-03-23 | American Laundry Machinery Incorporated | Durable press/wrinkle-free process |
WO1999058758A1 (en) * | 1998-05-11 | 1999-11-18 | The Procter & Gamble Company | Durable press/wrinkle-free process |
EP1141469A4 (en) * | 1998-09-30 | 2001-11-07 | Procter & Gamble A G | TEXTILE APPARATUS |
WO2001073185A3 (en) * | 2000-03-29 | 2002-01-03 | Procter & Gamble | Methods for improving brightness of fabrics and fabrics of improved brightness |
WO2001073186A3 (en) * | 2000-03-29 | 2002-01-31 | Procter & Gamble | Methods for improving fibrillation or pill resistance of fabrics and fabrics with improved properties |
WO2001073184A3 (en) * | 2000-03-29 | 2002-01-31 | Procter & Gamble | Methods for improving water absorbency of fabrics and fabrics with improved properties |
US6375685B2 (en) | 1997-05-13 | 2002-04-23 | The Procter & Gamble Company | Textile finishing process |
WO2001073187A3 (en) * | 2000-03-29 | 2002-07-04 | Procter & Gamble | Methods for reducing fabric drying time and fabrics with improved properties |
US20030074741A1 (en) * | 2001-10-18 | 2003-04-24 | The Procter & Gamble Company | Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents |
US20030088923A1 (en) * | 2001-10-18 | 2003-05-15 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
US6565612B2 (en) * | 1998-09-30 | 2003-05-20 | The Procter & Gamble Company | Shrink resistant rayon fabrics |
US20030111633A1 (en) * | 2001-10-18 | 2003-06-19 | Gardner Robb Richard | Durable press treatment of fabric |
US20030110573A1 (en) * | 2001-10-18 | 2003-06-19 | The Procter & Gamble Company | Textile finishing compositon and methods for using same |
US20040104148A1 (en) * | 1999-08-20 | 2004-06-03 | Lomas David A. | Controllable space velocity reactor and process |
US6989035B2 (en) | 2001-10-18 | 2006-01-24 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
US7018422B2 (en) | 2001-10-18 | 2006-03-28 | Robb Richard Gardner | Shrink resistant and wrinkle free textiles |
US20080147026A1 (en) * | 2006-12-15 | 2008-06-19 | Jian Qin | Absorbent fiber with a low absorbent capacity and slow absorption rate |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3423167A (en) * | 1964-12-15 | 1969-01-21 | Fmc Corp | Wet state cross-linking of carboxyalkyl cellulose ether modified regenerated cellulose fibers |
CH466206A (de) * | 1966-08-26 | 1969-01-31 | Traitex Internat Ag Fuer Texti | Verfahren zur Veredelung von cellulosehaltigen Textilien |
US3653805A (en) * | 1968-09-24 | 1972-04-04 | Cotton Inc | Delayed cure process using formaldehyde vapor to cause creaseproofing |
US3660013A (en) * | 1969-08-01 | 1972-05-02 | Mc Graw Edison Co | Method and apparatus for producing a durable press in garments containing cellulose or cellulosic derivatives |
US3703773A (en) * | 1970-04-09 | 1972-11-28 | Burlington Industries Inc | Gas phase reactor |
US3642428A (en) * | 1970-04-27 | 1972-02-15 | Cotton Inc | Vapor phase resin fixation process for cellulosic material permitting subsequent cure |
AT361888B (de) * | 1977-03-21 | 1981-04-10 | Chemiefaser Lenzing Ag | Nassvernetzte faser auf cellulosebasis und ver- fahren zu deren herstellung |
CA1340299C (en) * | 1986-06-27 | 1999-01-05 | Jeffrey Tood Cook | Process for marking individualized crosslinked fibers and fibers thereof |
IL82915A (en) * | 1986-06-27 | 1991-05-12 | Buckeye Cellulose Corp | Individualized,crosslinked fibers and their production |
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US3154373A (en) * | 1962-04-02 | 1964-10-27 | John D Guthrie | Process for treating cellulosic textiles with formaldehyde in vapor form |
US3175874A (en) * | 1959-01-29 | 1965-03-30 | Deering Milliken Res Corp | Method of creaseproofing cellulosic fabrics by wet creaseproofing followed by dry creaseproofing and the resulting product |
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-
0
- NL NL286002D patent/NL286002A/xx unknown
-
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- 1962-11-27 GB GB44777/62A patent/GB980980A/en not_active Expired
- 1962-11-28 DE DE1444129A patent/DE1444129C3/de not_active Expired
-
1968
- 1968-03-06 US US711136A patent/US3663974A/en not_active Expired - Lifetime
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US3189404A (en) * | 1960-10-13 | 1965-06-15 | Toyo Boseki | Treatment of cellulosic fibre fabrics |
US3154373A (en) * | 1962-04-02 | 1964-10-27 | John D Guthrie | Process for treating cellulosic textiles with formaldehyde in vapor form |
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Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3837799A (en) * | 1968-09-24 | 1974-09-24 | Cotton Inc | Process for creaseproofing cellulosic fiber-containing fabric using formaldehyde vapor and a solid and a solid catalyst |
US3841832A (en) * | 1971-12-06 | 1974-10-15 | Cotton Inc | Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide |
USRE30860E (en) * | 1971-12-06 | 1982-02-02 | Cotton, Incorporated | Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide |
US3884632A (en) * | 1973-03-14 | 1975-05-20 | Mc Graw Edison Co | Continuous durable-press processing of fabric and garments |
US3951595A (en) * | 1974-07-10 | 1976-04-20 | Mcgraw-Edison Company | Vapor phase process for cellulose fabrics |
US4108598A (en) * | 1976-12-02 | 1978-08-22 | The Strike Corporation | Durable press process |
US4269603A (en) * | 1979-05-04 | 1981-05-26 | Riegel Textile Corporation | Non-formaldehyde durable press textile treatment |
US4269602A (en) * | 1979-05-07 | 1981-05-26 | Riegel Textile Corporation | Buffered non-formaldehyde durable press textile treatment |
US4396390A (en) * | 1981-09-04 | 1983-08-02 | Springs Mills, Inc. | Aqueous formaldehyde textile finishing process |
US6528438B2 (en) * | 1997-05-13 | 2003-03-04 | The Procter & Gamble Company | Durable press/wrinkle-free process |
US5885303A (en) * | 1997-05-13 | 1999-03-23 | American Laundry Machinery Incorporated | Durable press/wrinkle-free process |
US6716255B2 (en) * | 1997-05-13 | 2004-04-06 | The Procter & Gamble Company | Textile finishing process |
US6719809B2 (en) * | 1997-05-13 | 2004-04-13 | The Procter & Gamble Company | Textile finishing process |
US6827746B2 (en) | 1997-05-13 | 2004-12-07 | Strike Investments, Llc | Textile finishing process |
US6375685B2 (en) | 1997-05-13 | 2002-04-23 | The Procter & Gamble Company | Textile finishing process |
US6121167A (en) * | 1997-08-22 | 2000-09-19 | Okamoto; Hiroharu | Moisture-controlled curing durable press process |
WO1999010589A1 (en) * | 1997-08-22 | 1999-03-04 | Hiroharu Okamoto | Moisture-controlled curing durable press process |
WO1999058758A1 (en) * | 1998-05-11 | 1999-11-18 | The Procter & Gamble Company | Durable press/wrinkle-free process |
US6511928B2 (en) | 1998-09-30 | 2003-01-28 | The Procter & Gamble Company | Rayon fabric with substantial shrink-resistant properties |
US6565612B2 (en) * | 1998-09-30 | 2003-05-20 | The Procter & Gamble Company | Shrink resistant rayon fabrics |
CN1594716B (zh) * | 1998-09-30 | 2010-07-21 | 斯特赖克投资有限责任公司 | 纺织整理方法 |
EP1141469A4 (en) * | 1998-09-30 | 2001-11-07 | Procter & Gamble A G | TEXTILE APPARATUS |
US20040104148A1 (en) * | 1999-08-20 | 2004-06-03 | Lomas David A. | Controllable space velocity reactor and process |
WO2001073187A3 (en) * | 2000-03-29 | 2002-07-04 | Procter & Gamble | Methods for reducing fabric drying time and fabrics with improved properties |
WO2001073184A3 (en) * | 2000-03-29 | 2002-01-31 | Procter & Gamble | Methods for improving water absorbency of fabrics and fabrics with improved properties |
WO2001073185A3 (en) * | 2000-03-29 | 2002-01-03 | Procter & Gamble | Methods for improving brightness of fabrics and fabrics of improved brightness |
WO2001073186A3 (en) * | 2000-03-29 | 2002-01-31 | Procter & Gamble | Methods for improving fibrillation or pill resistance of fabrics and fabrics with improved properties |
US7008457B2 (en) | 2001-10-18 | 2006-03-07 | Mark Robert Sivik | Textile finishing composition and methods for using same |
US20060085920A1 (en) * | 2001-10-18 | 2006-04-27 | Scheper William M | Textile finishing composition and methods for using same |
US20030088923A1 (en) * | 2001-10-18 | 2003-05-15 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
US6841198B2 (en) | 2001-10-18 | 2005-01-11 | Strike Investments, Llc | Durable press treatment of fabric |
US6989035B2 (en) | 2001-10-18 | 2006-01-24 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
US20030111633A1 (en) * | 2001-10-18 | 2003-06-19 | Gardner Robb Richard | Durable press treatment of fabric |
US7018422B2 (en) | 2001-10-18 | 2006-03-28 | Robb Richard Gardner | Shrink resistant and wrinkle free textiles |
US20030074741A1 (en) * | 2001-10-18 | 2003-04-24 | The Procter & Gamble Company | Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents |
US20060090266A1 (en) * | 2001-10-18 | 2006-05-04 | Gardner Robb R | Shrink resistant and wrinkle free textiles |
US20060090267A1 (en) * | 2001-10-18 | 2006-05-04 | Sivik Mark R | Textile finishing composition and methods for using same |
US7144431B2 (en) | 2001-10-18 | 2006-12-05 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
US7169742B2 (en) | 2001-10-18 | 2007-01-30 | The Procter & Gamble Company | Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents |
US7247172B2 (en) | 2001-10-18 | 2007-07-24 | The Procter & Gamble Company | Shrink resistant and wrinkle free textiles |
US20030110573A1 (en) * | 2001-10-18 | 2003-06-19 | The Procter & Gamble Company | Textile finishing compositon and methods for using same |
US20080147026A1 (en) * | 2006-12-15 | 2008-06-19 | Jian Qin | Absorbent fiber with a low absorbent capacity and slow absorption rate |
Also Published As
Publication number | Publication date |
---|---|
GB980980A (en) | 1965-01-20 |
DE1444129C3 (de) | 1975-04-17 |
DE1444129A1 (de) | 1968-11-07 |
NL286002A (en, 2012) |
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